CN102083775B - 稠合多环化合物和具有该化合物的有机发光器件 - Google Patents
稠合多环化合物和具有该化合物的有机发光器件 Download PDFInfo
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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Abstract
Description
技术领域
本发明涉及新型的稠合多环化合物和具有该化合物的有机发光器件。
背景技术
有机发光器件是具有薄膜的器件,该薄膜含有荧光或磷光有机化合物并且夹持在阳极和阴极之间;并且从各个电极注入空穴和电子。
然后,生成荧光或磷光化合物的激子。当该激子返回其基态时该激子辐射光。器件利用该光。
有机发光器件的最近进展显著,并且器件的特性使低外加电压下具有高亮度、各种发射波长、高速响应性、形状薄和重量轻的发光器件成为可能。由该事实,预示器件具有在各种用途中使用的潜力。
但是,目前的形势需要具有更高亮度或更高转换效率的光学输出。此外,仍存在许多与对于因长期使用而引起的经时变化、因含有氧、湿气等的氛围气而引起的劣化的耐久性有关的有待解决的问题。
此外,当考虑应用于全色显示器等时,对于与具有高色纯度的蓝色、绿色和红色的发光的需求有关的问题,现有技术仍不足。因此,需要用于实现具有良好的色纯度、高发光效率和良好的耐久性的有机发光器件的材料。
发明内容
本发明的目的是提供新型稠合多环化合物。本发明的另一目的是提供具有该新型稠合多环化合物的有机发光器件。该有机发光器件具有高效率和高亮度的光学输出并且具有耐久性。
本发明提供由以下通式(I)表示的稠合多环化合物:
其中R1-R18各自独立地选自氢原子、卤素原子、氰基基团、硝基基团、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的氨基基团、取代或未取代的芳基和取代或未取代的杂环基。
本发明的通式(I)表示的化合物能够提供用于具有优异的发光特性和高稳定性的有机发光器件的材料,并因此能够提供具有极高效率和极高亮度的光学输出并且极其耐久的有机发光器件。
由以下参照附图对示例性实施方案的说明,本发明进一步的特征将变得清楚。
附图说明
图1是表示本发明中的有机发光器件的实例的截面图。
图2是表示本发明中的有机发光器件的另一实例的截面图。
图3是表示本发明中的有机发光器件的另一实例的截面图。
图4是表示本发明中的有机发光器件的另一实例的截面图。
图5是表示本发明中的有机发光器件的另一实例的截面图。
图6是表示示例化合物3-15在甲苯中的溶液(1×10-6mol/l)的荧光光谱(激发波长:360nm)的图。
图7是表示示例化合物3-7在甲苯中的溶液(1×10-6mol/l)的荧光光谱(激发波长:360nm)的图。
具体实施方式
根据本发明的新型稠合多环化合物是由以下通式(I)表示的稠合多环化合物:
其中R1-R18各自独立地选自氢原子、卤素原子、氰基基团、硝基基团、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的氨基基团、取代或未取代的芳基和取代或未取代的杂环基。
通式(I)中稠合多环化合物的取代基的具体实例如下所示,但并不限于此。
R1-R18的具体实例如下所示。
卤素原子的实例包括氟、氯、溴和碘。
烷基的实例包括甲基、乙基、正丙基、异丙基、正丁基、叔丁基、仲丁基、辛基、1-金刚烷基和2-金刚烷基。
烷氧基的实例包括甲氧基、乙氧基、丙氧基和苯氧基。
烯基的实例包括乙烯基、丙烯基、丁烯基、苯基乙烯基和二苯基乙烯基。
炔基的实例包括乙炔基、丙炔基、丁炔基和苯乙炔基。
芳烷基的实例包括苄基和苯乙基。
氨基基团的实例包括二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基、二叔丁基氨基、二(茴香醚基)氨基、萘基苯基氨基和咔唑基。
芳基的实例包括苯基、萘基、并环戊二烯基、茚基、薁基、蒽基、芘基、苯并二茚基、苊基、菲基、1,8-苯嵌萘基、荧蒽基、苯并荧蒽基、醋菲基、醋蒽基、苯并[9,10]菲基、基、并四苯基、苝基、并五苯基、联苯基、三联苯基和芴基。
烷基、烷氧基、烯基、炔基、芳烷基、氨基基团、芳基和杂环基可均具有取代基。取代基的实例包括:
烷基例如甲基、乙基、丙基和叔丁基;芳烷基例如苄基和苯乙基;
芳基例如苯基、联苯基、萘基、芘基、蒽基和芴基;
杂环基例如噻吩基、吡咯基、吡啶基、phenanthroryl基和咔唑基;
氨基基团例如二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基和二(茴香醚基)氨基;
烷氧基例如甲氧基、乙氧基、丙氧基和苯氧基;
氰基基团;硝基基团;和卤素原子例如氟和氯。
通式(I)所示的稠和多环化合物能够主要用作有机发光器件的材料。
特别地,通式(I)所示的化合物能够用于空穴传输层、电子传输层或发光层中以提供具有高发光效率和长寿命的器件。
此外,当通式(I)所示的稠合多环化合物在发光层中使用时,能够以各种方式中的任一种使用该化合物以提供具有高色纯度、高发光效率和长寿命的器件。
例如,该化合物可以在发光层中单独使用。或者,该化合物可在发光层中用作掺杂剂(客体)材料。或者,该化合物可用作荧光材料和磷光材料的每一种的主体材料。
当通式(I)所示的稠合多环化合物用作客体时,该化合物的含量优选为0.1wt%-30wt%,相对于发光层的总重量;为了可抑制浓度猝灭,该含量更优选为0.1wt%-15wt%。
此外,当通式(I)所示的稠合多环化合物用作客体时,对主体材料并无特别限制;为了可提供由稳定的无定形膜形成的有机发光器件,优选使用稠合多环衍生物。此外,为了可提供具有高效率并且耐久的有机发光器件,要求主体材料自身具有高发光效率,或者要求主体自身具有化学稳定性。因此,更优选具有高荧光量子效率和化学稳定性的稠合多环衍生物例如芴衍生物、芘衍生物、荧蒽衍生物或苯并荧蒽衍生物。
另一方面,当通式(I)所示的稠合多环化合物用作主体化合物时,对客体并无特别限制,并且只需根据例如所需的发射色来适当使用客体。此外,可根据需要已用空穴传输性化合物、电子传输性化合物等以及客体掺杂后使用该化合物。
为了可改善有机发光器件的发光效率,希望发光中心材料(客体)自身的发射量子效率大。此外,当将有机发光器件应用于显示设备时,对于发光中心材料重要的是具有高色纯度。
通常,在等于或高于室温的温度下,许多有机化合物均显示宽的荧光光谱,并且均倾向于具有差的色纯度。鉴于上述内容,在稠合多环化合物中已进行了以下分子设计:将共轭体系扩展以致可使振动结构出现在化合物的光谱上,并且可增加化合物的色纯度。
但是,将上述方法应用于具有大能量的蓝色荧光并不容易,原因在于共轭体系的扩展涉及能隙的变窄。
鉴于上述内容,本发明的发明人进行了广泛研究。结果,发明人已发现通式(I)所示的稠合多环化合物显示具有显著的振动结构的荧光光谱,并且产生具有高蓝色色纯度的荧光发射。即,通过使用萘环作为用于与骨架形成五元环的两个芳环中的一个并且使用苯环作为这两个芳环中的另一个而将共轭体系适当地扩展。以这样的程序,使作为0-0迁移的第一峰的相对强度比任何其他峰的相对强度强,并且使光谱的半宽度变窄,由此在无光谱从蓝色区域偏离的情况下能够实现色纯度的增加。
此外,通式(I)所示的稠合多环化合物适合制备具有高效率和高色纯度的蓝色有机发光器件,原因在于该化合物具有由其刚性骨架导致的高量子效率。
为了可提供耐久的有机发光器件,构成器件的用于有机发光器件的化合物必须具有化学稳定性。
通式(I)所示的稠合多环化合物,由于每一个五元环结构的吸电子效应而具有基于例如单态氧分子的亲电反应的低反应性,并且因此化学稳定。此外,该具有两个五元环结构的化合物具有比具有一个五元环结构的骨架例如荧蒽或苯并荧蒽的骨架高的化学稳定性。
通式(I)所示的稠合多环化合物由于每一个五元环结构的吸电子性而具有电子注入性。结果,当该化合物用作有机发光器件用材料时,能够降低驱动器件的电压。此外,该具有两个五元环结构的化合物与具有一个五元环结构的骨架例如荧蒽或苯并荧蒽的骨架相比,对驱动器件的电压发挥更高的降低效果。
通式(I)所示的化合物的HOMO/LUMO能级能够通过引入取代基而容易地调节。
因此,能够考虑注入的载流子例如空穴和电子的量之间的平衡来进行分子设计。此外,能够进行用于各种发射色的发光材料的分子设计。
此外,当通式(I)中的R1-R18的至少一个表示取代基时,该取代基的存在导致对稠合多环化合物的分子的重叠的避免效果,并且有助于:化合物的升华性和沉积稳定性;和由于化合物的结晶性的降低或者该化合物的高玻璃化转变温度导致的该化合物制成的膜的稳定性。由R1-R18中的至少一个表示的取代基优选是取代或未取代的芳基、或者取代或未取代的杂环基;R1、R4、R9和R14均更优选表示取代或未取代的芳基、或者取代或未取代的杂环基。特别地,当取代基进入R1、R4、R9和R14的每一个时,取代基的任一个与邻近基团的空间位阻太大以致对分子的重叠的避免效果变大。
基于如上所述的讨论,已通过分子设计完成了本发明。
以下对本发明更详细地说明。
通式(I)表示的上述稠合多环化合物的具体实例如下所示。但是,本发明并不限于这些实例。
化合物实例1
化合物实例2
化合物实例3
其次,对本发明的有机发光器件更详细地说明。
本发明的有机发光器件包括由阳极和阴极组成的一对电极、和夹持在该对电极之间的有机化合物层。该有机发光器件中,该有机化合物层至少含有根据本发明的稠合多环化合物。
图1-5均表示本发明的有机发光器件的优选的实例。
首先,对每个附图标记进行说明。
设置基板1、阳极2、发光层3、阴极4、空穴传输层5、电子传输层6、空穴注入层7和空穴/激子阻挡层8。
图1是表示根据本发明的有机发光器件的实例的截面图。如图1中所示,有机发光器件具有如下结构,其中按所述顺序在基板1上设置阳极2、发光层3和阴极4。这里使用的发光器件在器件自身具有空穴传输性、电子传输性和发光性或者将具有各个性能的化合物组合使用的情况下有用。
图2是表示根据本发明的有机发光器件的另一实例的截面图。如图2中所示,有机发光器件具有如下结构,其中按所述顺序在基板1上设置阳极2、空穴传输层5、电子传输层6和阴极4。在将具有空穴传输性和电子传输性中的一者或两者的材料用于每一层并且将发光物质与非发光空穴传输物质或电子传输物质组合使用的情况下,发光物质有用。在这种情况下,发光层3由空穴传输层5或电子传输层6构成。
图3是表示根据本发明的有机发光器件的又一实例的截面图。如图3中所示,有机发光器件具有如下结构,其中按所述顺序在基板1上设置阳极2、空穴传输层5、发光层3、电子传输层6和阴极4。该有机发光器件具有分离的载流子传输功能和发光功能。与均具有适当的空穴传输性、电子传输性或发光性的化合物组合使用该器件,由此使待使用的材料的选择自由度显著增加。此外,能够使用具有不同发射波长的各种化合物,由此使发射色调的种类增加。此外,通过在器件的中间设置的发光层3中高效地捕集每一个载流子或激子,可改善发光效率。
图4是表示根据本发明的有机发光器件的又一实例的截面图。图4具有图3中所示的结构,不同之处在于将空穴注入层7插入阳极2侧。这种结构对于改善阳极2和空穴传输层5之间的粘合性或者对于改善空穴注入性有效,其在降低对器件施加的电压方面有效。
图5是表示根据本发明的有机发光器件的又一实例的截面图。图5具有图3中所示的结构,不同之处在于在发光层3和电子传输层6之间插入用于阻挡空穴或激子向阴极4侧迁移的层(空穴/激子阻挡层8)。这种结构将具有极高电离电位的化合物用于空穴/激子阻挡层8并且对于改善发光效率有效。
应指出的是,图1-5均表示基本器件结构,并且使用本发明的化合物的有机发光器件的结构并不限于图1-5中所示的结构。例如,本发明的有机发光器件可具有各种层结构中的任一种,该各种层结构包括:其中在电极和有机层之间的界面处设置绝缘层的结构;其中设置粘合层或干涉层的结构;和其中空穴传输层由具有不同电离电位的两层组成的结构。
通式(I)所示并且在本发明中使用的稠合多环化合物可用于图1-5中所示结构的任一种。
特别地,通过真空沉积法、溶液涂布法等形成使用本发明化合物的有机层时,该层难以结晶并且具有优异的经时稳定性。
本发明中,通式(I)所示的稠合多环化合物特别用作发光层的组分。此外,可根据需要将以往已知的化合物例如低分子量类或聚合物类空穴传输性化合物、发光化合物或电子传输性化合物一起使用。
空穴传输性化合物的实例包括:三芳基胺衍生物、苯二胺衍生物、三唑衍生物、二唑衍生物、咪唑衍生物、吡唑啉衍生物、吡唑啉酮衍生物、唑衍生物、芴酮衍生物、腙衍生物、1,2-二苯乙烯衍生物、酞菁衍生物、卟啉衍生物、聚(乙烯基咔唑)、聚(亚甲硅烷基)(poly(silylene))、聚(噻吩)和其他导电聚合物。
本发明的稠环芳族化合物之外的发光化合物的实例包括:萘衍生物、菲衍生物、芴衍生物、芘衍生物、并四苯衍生物、晕苯衍生物、衍生物、苝衍生物、9,10-二苯基蒽衍生物、红荧烯、喹吖啶酮衍生物、吖啶酮衍生物、香豆素衍生物、吡喃衍生物、尼罗红、吡嗪衍生物、苯并咪唑衍生物、苯并噻唑衍生物、苯并唑衍生物、和1,2-二苯乙烯衍生物、有机金属络合物(例如,有机铝络合物例如三(8-羟基喹啉合)铝、和有机铍络合物)、和聚合物衍生物,该聚合物衍生物包括聚(亚苯基亚乙烯基)衍生物、聚(芴)衍生物、聚(亚苯基)衍生物、聚(亚噻吩基亚乙烯基)衍生物和聚(乙炔)衍生物。
电子传输性化合物的实例包括二唑衍生物、唑衍生物、噻唑衍生物、噻二唑衍生物、吡嗪衍生物、三唑衍生物、三嗪衍生物、苝衍生物、喹啉衍生物、喹喔啉衍生物、芴酮衍生物、蒽酮衍生物、菲绕啉衍生物和有机金属络合物。
构成阳极的材料的实例包括:金属单质例如金、铂、银、铜、镍、钯、钴、硒、钒或钨;它们的合金;和金属氧化物例如氧化锡、氧化锌、氧化铟、氧化铟锡(ITO)或氧化铟锌。此外,也可使用导电聚合物例如聚苯胺、聚吡咯、聚噻吩或聚苯硫醚。这些电极材料的每一种可单独使用,或者可将它们的两种以上组合使用。此外,阳极可具有单层结构或多层结构。
构成阴极的材料的实例包括:金属单质例如锂、钠、钾、钙、镁、铝、铟、钌、钛、锰、钇、银、铅、锡或铬;和它们的合金例如锂-铟合金、钠-钾合金、镁-银合金、铝-锂合金、铝-镁合金或镁-铟合金。也可使用金属氧化物例如氧化铟锡(ITO)。这些电极材料的每一种可单独使用或者可将其两种以上组合使用。此外,阴极可具有单层结构或多层结构。
对本发明中使用的基板并无特别限制,但其实例包括:不透明基板例如金属基板或陶瓷基板;和透明基板例如玻璃基板、石英基板或塑料片材基板。
此外,基板可以具有用于控制发光色的滤色膜、荧光色变换滤色膜、介电反射膜等。此外,在基板上可制备薄膜晶体管(TFT)作为开关器件,然后通过与该TFT连接可制备能够控制发光的开/关的器件。在这种情况下,容许所谓的有源驱动。当然,根据本发明的有机发光器件是否发光可由所谓的无源驱动(简单矩阵驱动)控制。
或者,根据本发明的有机发光器件可通过duty drive和staticdrive之一驱动。
关于器件的发光方向,该器件可具有底部发光结构(从基板侧发光的结构)或顶部发光结构(从基板的相反侧发光的结构)。
此外,可采用以下程序:将多个根据本发明的有机发光器件放置在相同的基板上并且均用作像素。在这种情况下,可进一步设置用于控制每个像素的控制单元。此外,在这种情况下,能够提供在其像素部的任一个具有任何这样的有机发光器件作为像素的显示装置。显示装置为例如薄显示器。或者,显示装置可在电子照相成像装置的操作部中使用。
如上所述,本发明的有机发光器件能够用于各种装置的任一种。各种装置的实例包括如上所述的显示器和电子照相成像装置。实例进一步包括成像装置例如数码照相机和数码摄像机。或者,有机发光器件,例如,可安装在显示器上,该显示器安装在车辆例如汽车(例如四轮汽车或两轮汽车)或火车中。或者,能够提供具有有机发光器件作为其光源的照明装置或者具有有机发光器件作为曝光光源的电子照相成像装置。
以下参照实施例对本发明更具体地说明,但本发明并不限于实施例。
<实施例1>
示例化合物3-15的合成
(a)中间化合物4-1的合成
将20.0g(87.6mmol)的46.7g(350mmol)的氯化铝和400ml的二氯甲烷装入500-ml三颈烧瓶中。在氮气氛中在-78℃下搅拌混合物的同时,将55.6g(438mmol)的草酰氯滴入该混合物。然后,对得到的混合物搅拌30分钟,随后用2小时将其温度升高到室温。将反应溶液装入4升的冰水中,同时对冰水进行搅拌。通过过滤分离得到的固体,然后分散在100ml甲醇中并用其进行洗涤。将该固体过滤并通过在真空中进行加热而将其干燥,由此得到21.5g的中间化合物4-1(橙色粉末)(87%收率)。
(b)中间化合物4-3的合成
将2.01g(7.10mmol)的化合物4-1、1.50g(7.13mmol)的化合物4-2和100ml的乙醇装入200-ml三颈烧瓶中。在氮气氛中在室温下搅拌混合物的同时,将已溶解了4.00g的氢氧化钾的25ml水溶液滴入混合物中。其次,将得到的混合物的温度升高到75℃,然后将该混合物搅拌1小时30分钟。将反应液体已冷却后,通过过滤分离沉淀的固体并干燥,由此得到3.08g的中间化合物4-3(绿色粉末)(95%收率)。
(c)中间化合物4-4的合成
将4.00g(8.76mmol)的化合物4-3、1.26g(9.19mmol)的氨茴酸、1.50ml(11.2mmol)的亚硝酸异戊酯和300ml的甲苯装入500-ml三颈烧瓶中。在氮气氛中,将混合物的温度升高到85℃,然后将该混合物搅拌2小时。已将反应液体冷却后,向该反应液体添加水,并且对该混合物进行两相萃取。用无水硫酸钠将有机相干燥,然后用硅胶柱(使用甲苯和庚烷的混合物作为展开溶剂)进行纯化,由此得到2.27g的中间化合物4-4(黄色粉末)(51%收率)。
(d)中间化合物4-5的合成
将1.00g(1.98mmol)的化合物4-4、1.06g(7.92mmol)的氯化铝和50ml的二氯甲烷装100-ml三颈烧瓶中。在氮气氛中在-78℃下搅拌该混合物的同时,向该混合物滴加1.26g(9.90mmol)的草酰氯。然后,将得到的混合物搅拌30分钟,随后,用2小时将其温度升高到室温。将该反应溶液倒入1升的冰水中,同时搅拌该冰水。通过过滤分离得到的固体,然后分散在30ml的甲醇中并用其进行洗涤。过滤固体并且通过在真空中加热来将其干燥,由此得到1.11g的中间化合物4-5(橙色粉末)(100%收率)。
(e)中间化合物4-7的合成
将1.11g(1.98mmol)的化合物4-5、0.856g(1.97mmol)的化合物4-6、100ml的乙醇和10ml的甲苯装入200-ml三颈烧瓶中。在氮气氛中在室温下搅拌该混合物的同时,向该混合物滴加已溶解了1.11g的氢氧化钾的5ml的水溶液。其次,将得到的混合物的温度升高到75℃,然后将该混合物搅拌1小时30分钟。已将该反应液体冷却后,通过过滤分离沉淀的固体并将其干燥,由此得到0.87g的中间化合物4-7(绿色粉末)(46%收率)。
(f)示例化合物3-15的合成
将0.87g(0.91mmol)的化合物4-7、8.38g(91mmol)的2,5-降冰片二烯和40ml的醋酸酐装入200-ml三颈烧瓶中。在氮气氛中,将该混合物的温度升高到90℃,然后将该混合物搅拌18小时。将该混合物冷却到室温,并且通过减压下的蒸馏将溶剂除去。然后,用硅胶柱(使用甲苯和庚烷的混合物作为展开溶剂)将残留物纯化,由此得到0.25g的示例化合物3-15(黄色粉末)(29%收率)。
质谱确认该化合物的M+与示例化合物3-15相同,即为955。
此外,通过将激发波长设定为360nm,用荧光分光光度计(由Hitachi,Ltd.制造的F-4500)测定浓度为10-6mol/l的该化合物在甲苯中的稀溶液的发射光谱。作为测定的结果,得到图6中所示的荧光光谱,并且该化合物显示在464nm具有发射局部最大值的良好的蓝色发光。
<实施例2>
示例化合物3-7的合成
通过与实施例1相同的合成方法合成示例化合物3-7;具体地,在与实施例1相同的条件下进行合成,不同之处是将实施例1中的化合物4-6变为化合物4-2。
质谱确认该化合物的M+与示例化合物3-7相同,即为730。
此外,通过将激发波长设定为360nm,测定浓度为10-6mol/l的该化合物在甲苯中的稀溶液的发射光谱。作为测定的结果,得到图7中所示的荧光光谱,并且该化合物显示在463nm具有发射局部最大值的良好的蓝色发光。
以下可通过与实施例1相同的合成方法合成示例化合物2-5、2-9、3-13、3-14、3-16、3-17、3-18、3-19、3-25和3-26中的每一个;具体地,在与实施例1相同的条件下进行合成,不同之处是代替实施例1中的化合物4-2(第一酮衍生物)和化合物4-6(第二酮衍生物)而使用下表1中所示的酮衍生物。
<实施例3>
有机发光器件的制备
在实施例3中,制备图3中所示的有机发光器件。首先,在玻璃基板(基板1)上用厚度为100nm的氧化铟锡(ITO)(阳极2)进行图案化,以由此制备具有ITO电极的玻璃基板。依次用丙酮和异丙醇(IPA)对该具有ITO电极的玻璃基板进行超声波清洁。然后,用IPA对基板进行煮沸清洁,接着干燥,并且进一步进行UV/臭氧清洁。将这样处理的基板用作透明导电支持基板。
其次,通过基于电阻加热的真空气相沉积在具有ITO电极的玻璃基板上连续地形成均由有机化合物形成的层和阴极。具体地,首先,将以下所示的化合物A形成为厚度为20nm的层以充当空穴传输层5。其次,通过共沉积作为主体的以下所示的化合物B和作为客体的示例化合物3-15以使示例化合物3-15相对于化合物B的含量为1wt%来形成发光层3。在这种情况下,将发光层3的厚度设定为30nm。其次,将以下所示的化合物C形成为厚度30nm的层以充当电子传输层6。其次,将KF形成为厚度1nm的层以充当第一金属电极层。最后,将Al形成为厚度100nm的层以充当第二金属电极层。其中,KF和Al共同作为阴极4发挥作用。
应指出的是,层形成时真空室内的压力设定为10-5Pa。此外,制备器件时均使对置电极具有3mm2的面积。这样得到有机发光器件。
对得到的有机发光器件的特性进行测定和评价。具体地,用由Hewlett-Packard Company制造的微安计4140B测定器件的电流-电压特性,并且用由TOPCON CORPORATION制造的BM7测定器件的发射亮度。结果,观察到器件显示在4.0V的外加电压下具有420cd/m2的发射亮度的良好的蓝色发光。此外,在氮气氛下对该器件外加电压100小时。结果,观察到该器件继续良好的发光。
尽管已参照示例性实施方案对本发明进行了说明,但应理解本发明并不限于公开的示例性实施方案。以下权利要求的范围应给予最宽泛的解释以包括所有这样的变形和等同结构及功能。
本申请要求2008年5月22日提交的日本专利申请No.2008-134318的权益,在此通过引用将其全文并入本文。
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JP5414258B2 (ja) * | 2008-12-10 | 2014-02-12 | キヤノン株式会社 | ベンゾインデノクリセン化合物及びこれを用いた有機発光素子 |
JP5709382B2 (ja) | 2009-03-16 | 2015-04-30 | キヤノン株式会社 | 新規クリセン化合物及びこれを有する有機発光素子 |
JP4721475B2 (ja) * | 2009-10-01 | 2011-07-13 | キヤノン株式会社 | ジインデノピセン化合物及びこれを使用した有機発光素子 |
JP4830029B2 (ja) * | 2010-02-02 | 2011-12-07 | キヤノン株式会社 | 新規有機化合物およびそれを有する有機発光素子 |
JP5578934B2 (ja) * | 2010-05-19 | 2014-08-27 | キヤノン株式会社 | 新規有機化合物 |
JP5669539B2 (ja) | 2010-12-01 | 2015-02-12 | キヤノン株式会社 | キノリノ[3,2,1−kl]フェノキサジン化合物及びこれを用いた有機発光素子 |
JP5669550B2 (ja) | 2010-12-10 | 2015-02-12 | キヤノン株式会社 | インドロフェノキサジン化合物及びこれを用いた有機発光素子 |
CN103475726B (zh) * | 2013-09-17 | 2017-03-15 | 北京京东尚科信息技术有限公司 | 一种虚拟桌面管理方法、服务器和客户端 |
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